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Zimbra

Silicon Valley VC Redpoint Ventures, which is leading the Series A investment round, is convinced that Expensify co-founder David Barrett's strategy of getting small-biz employees hooked on its expense-report smartphone apps is the key to a huge market.

Yahoo failed to capitalize on Zimbra's dynamic email and collaboration software, so VMware must be betting it can do better. But in moving into the highly competitive application sector, VMware will face the likes of Google, IBM, Citrix and of course, Microsoft.